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The asymmetric unit of the title compound, [Cu(C15H10N3O4S)2], contains one half-mol­ecule. The other half of the complex mol­ecule is related by a C2 axis running through the Cu atom. The Cu atom is four-coordinated by two quinoline N and two sulfonamide N atoms. In the crystal structure, the mol­ecules are linked through inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004867/bt2004sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004867/bt2004Isup2.hkl
Contains datablock I

CCDC reference: 601117

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.071
  • wR factor = 0.202
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.108 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT213_ALERT_2_C Atom O4 has ADP max/min Ratio ............. 3.10 prolat PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.61 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C1 .. 2.94 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 47.00 A   3 PLAT733_ALERT_1_C Torsion Calc -29.1(6), Rep -29.15(19) ...... 3.16 su-Rat S1 -N1 -CU1 -N1 1.555 1.555 1.555 2.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4-PC (Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Bis[4-nitro-N-(quinolin-8-yl)benzenesulfonamidato-κ2N,N']copper(II) top
Crystal data top
[Cu(C15H10N3O4S)2]F(000) = 1468
Mr = 720.18Dx = 1.567 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 14.101 (2) Åθ = 4.1–22.8°
b = 16.823 (2) ŵ = 2.83 mm1
c = 13.172 (2) ÅT = 299 K
β = 102.35 (1)°Prism, dark green
V = 3052.4 (7) Å30.38 × 0.13 × 0.10 mm
Z = 4
Data collection top
Nonius CAD-4
diffractometer
2074 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.108
Graphite monochromatorθmax = 67.0°, θmin = 4.2°
ω/2θ scansh = 1616
Absorption correction: ψ scan
(North et al., 1968)
k = 2020
Tmin = 0.556, Tmax = 0.789l = 150
5582 measured reflections3 standard reflections every 120 min
2720 independent reflections intensity decay: 5.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.202 w = 1/[σ2(Fo2) + (0.1447P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2720 reflectionsΔρmax = 1.00 e Å3
214 parametersΔρmin = 1.58 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (3)
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1090 (3)0.1940 (3)0.0526 (3)0.0414 (10)
H10.05380.20090.02570.050*
C20.1887 (3)0.1521 (3)0.0063 (3)0.0484 (11)
H20.18530.13080.07060.058*
C30.2708 (3)0.1432 (3)0.0316 (4)0.0494 (11)
H30.32390.11620.00730.059*
C40.2753 (3)0.1749 (3)0.1302 (3)0.0417 (10)
C50.3575 (3)0.1702 (3)0.1746 (4)0.0544 (13)
H50.41370.14530.13910.065*
C60.3539 (3)0.2024 (3)0.2695 (4)0.0571 (13)
H60.40850.19910.29840.069*
C70.2693 (3)0.2414 (3)0.3268 (4)0.0489 (11)
H70.26870.26200.39250.059*
C80.1891 (3)0.2483 (3)0.2849 (3)0.0362 (9)
C90.1919 (3)0.2146 (2)0.1849 (3)0.0347 (9)
C100.1791 (3)0.4300 (3)0.1814 (3)0.0394 (9)
C110.2698 (3)0.4416 (3)0.1585 (4)0.0505 (12)
H110.28410.41940.09890.061*
C120.3383 (3)0.4861 (3)0.2248 (4)0.0499 (11)
H120.39970.49370.21110.060*
C130.3146 (3)0.5192 (3)0.3112 (3)0.0416 (10)
C140.2231 (3)0.5109 (3)0.3339 (3)0.0432 (10)
H140.20800.53540.39170.052*
C150.1561 (3)0.4656 (3)0.2683 (3)0.0417 (10)
H150.09460.45860.28200.050*
N10.1000 (2)0.2856 (2)0.1714 (3)0.0408 (9)
N20.1109 (2)0.2236 (2)0.1449 (3)0.0349 (8)
N30.3895 (3)0.5633 (3)0.3854 (3)0.0596 (11)
O10.0010 (2)0.3956 (2)0.0945 (2)0.0516 (8)
O20.1304 (3)0.3520 (3)0.0085 (2)0.0623 (11)
O30.3707 (3)0.5931 (3)0.4612 (3)0.0790 (13)
O40.4684 (3)0.5684 (4)0.3643 (5)0.134 (3)
S10.09590 (7)0.36405 (7)0.10305 (7)0.0411 (4)
Cu10.00000.26765 (5)0.25000.0348 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.037 (2)0.049 (3)0.035 (2)0.0041 (18)0.0004 (16)0.0021 (17)
C20.046 (2)0.052 (3)0.041 (2)0.005 (2)0.0054 (18)0.0085 (19)
C30.041 (2)0.045 (2)0.052 (3)0.0028 (19)0.0132 (19)0.0022 (19)
C40.030 (2)0.037 (2)0.051 (2)0.0032 (16)0.0057 (17)0.0101 (18)
C50.033 (2)0.064 (3)0.062 (3)0.011 (2)0.002 (2)0.017 (2)
C60.031 (2)0.072 (3)0.069 (3)0.009 (2)0.014 (2)0.019 (3)
C70.035 (2)0.067 (3)0.046 (2)0.002 (2)0.0106 (18)0.010 (2)
C80.0263 (18)0.044 (2)0.037 (2)0.0007 (15)0.0018 (15)0.0091 (16)
C90.0269 (18)0.037 (2)0.036 (2)0.0000 (15)0.0031 (15)0.0098 (15)
C100.033 (2)0.052 (3)0.0336 (19)0.0030 (18)0.0083 (15)0.0064 (17)
C110.040 (2)0.073 (3)0.045 (2)0.005 (2)0.0235 (19)0.003 (2)
C120.033 (2)0.058 (3)0.064 (3)0.0107 (19)0.024 (2)0.001 (2)
C130.034 (2)0.046 (2)0.047 (2)0.0092 (17)0.0111 (17)0.0022 (18)
C140.040 (2)0.054 (3)0.040 (2)0.0017 (19)0.0167 (17)0.0032 (19)
C150.0291 (19)0.059 (3)0.039 (2)0.0001 (18)0.0128 (16)0.0052 (18)
N10.0268 (16)0.061 (2)0.0326 (17)0.0007 (15)0.0019 (13)0.0002 (15)
N20.0265 (15)0.0417 (19)0.0328 (16)0.0047 (13)0.0018 (12)0.0039 (14)
N30.048 (2)0.070 (3)0.064 (3)0.022 (2)0.019 (2)0.015 (2)
O10.0304 (15)0.073 (2)0.0479 (17)0.0039 (15)0.0018 (12)0.0142 (16)
O20.062 (2)0.102 (3)0.0257 (15)0.010 (2)0.0153 (14)0.0020 (16)
O30.073 (3)0.105 (4)0.061 (2)0.031 (3)0.020 (2)0.021 (2)
O40.063 (3)0.181 (6)0.174 (5)0.069 (4)0.060 (3)0.115 (5)
S10.0305 (6)0.0654 (8)0.0269 (5)0.0015 (4)0.0054 (4)0.0041 (4)
Cu10.0212 (5)0.0528 (6)0.0285 (5)0.0000.0012 (3)0.000
Geometric parameters (Å, º) top
C1—N21.319 (5)C10—S11.776 (4)
C1—C21.410 (6)C11—C121.377 (7)
C1—H10.9300C11—H110.9300
C2—C31.363 (7)C12—C131.372 (6)
C2—H20.9300C12—H120.9300
C3—C41.418 (7)C13—C141.392 (5)
C3—H30.9300C13—N31.476 (5)
C4—C91.409 (5)C14—C151.367 (6)
C4—C51.409 (6)C14—H140.9300
C5—C61.353 (7)C15—H150.9300
C5—H50.9300N1—C8i1.413 (5)
C6—C71.429 (7)N1—S11.591 (4)
C6—H60.9300N1—Cu11.943 (3)
C7—C81.365 (6)N2—Cu11.996 (3)
C7—H70.9300N3—O31.198 (5)
C8—N1i1.413 (5)N3—O41.206 (6)
C8—C91.427 (6)O1—S11.448 (3)
C9—N21.364 (5)O2—S11.445 (3)
C10—C111.389 (6)Cu1—N1i1.943 (3)
C10—C151.391 (6)Cu1—N2i1.996 (3)
N2—C1—C2121.7 (4)C13—C12—C11118.9 (4)
N2—C1—H1119.1C13—C12—H12120.5
C2—C1—H1119.1C11—C12—H12120.5
C3—C2—C1119.5 (4)C12—C13—C14122.6 (4)
C3—C2—H2120.2C12—C13—N3119.1 (4)
C1—C2—H2120.2C14—C13—N3118.3 (4)
C2—C3—C4120.1 (4)C15—C14—C13117.9 (4)
C2—C3—H3120.0C15—C14—H14121.1
C4—C3—H3120.0C13—C14—H14121.1
C9—C4—C5119.0 (4)C14—C15—C10120.5 (4)
C9—C4—C3116.8 (4)C14—C15—H15119.7
C5—C4—C3124.1 (4)C10—C15—H15119.7
C6—C5—C4119.3 (4)C8i—N1—S1121.4 (3)
C6—C5—H5120.3C8i—N1—Cu1113.4 (3)
C4—C5—H5120.3S1—N1—Cu1119.2 (2)
C5—C6—C7122.3 (4)C1—N2—C9119.8 (4)
C5—C6—H6118.9C1—N2—Cu1127.8 (3)
C7—C6—H6118.9C9—N2—Cu1111.7 (3)
C8—C7—C6119.7 (5)O3—N3—O4122.9 (5)
C8—C7—H7120.2O3—N3—C13120.5 (4)
C6—C7—H7120.2O4—N3—C13116.7 (4)
C7—C8—N1i127.9 (4)O2—S1—O1118.0 (2)
C7—C8—C9118.6 (4)O2—S1—N1113.2 (2)
N1i—C8—C9113.5 (3)O1—S1—N1105.51 (19)
N2—C9—C4122.1 (4)O2—S1—C10106.6 (2)
N2—C9—C8116.9 (3)O1—S1—C10108.1 (2)
C4—C9—C8121.0 (4)N1—S1—C10104.47 (18)
C11—C10—C15120.4 (4)N1—Cu1—N1i162.1 (2)
C11—C10—S1119.0 (3)N1—Cu1—N2103.79 (14)
C15—C10—S1120.4 (3)N1i—Cu1—N282.95 (14)
C12—C11—C10119.5 (4)N1—Cu1—N2i82.95 (14)
C12—C11—H11120.2N1i—Cu1—N2i103.79 (14)
C10—C11—H11120.2N2—Cu1—N2i136.37 (19)
N2—C1—C2—C31.4 (7)C8—C9—N2—C1179.8 (4)
C1—C2—C3—C40.8 (7)C4—C9—N2—Cu1171.5 (3)
C2—C3—C4—C90.4 (6)C8—C9—N2—Cu19.3 (4)
C2—C3—C4—C5178.5 (5)C12—C13—N3—O3179.7 (5)
C9—C4—C5—C61.3 (7)C14—C13—N3—O32.2 (7)
C3—C4—C5—C6179.8 (5)C12—C13—N3—O40.8 (8)
C4—C5—C6—C70.1 (8)C14—C13—N3—O4178.9 (6)
C5—C6—C7—C81.2 (8)C8i—N1—S1—O263.5 (4)
C6—C7—C8—N1i178.8 (4)Cu1—N1—S1—O2145.6 (2)
C6—C7—C8—C91.2 (7)C8i—N1—S1—O1166.0 (3)
C5—C4—C9—N2177.8 (4)Cu1—N1—S1—O115.1 (3)
C3—C4—C9—N21.1 (6)C8i—N1—S1—C1052.1 (4)
C5—C4—C9—C81.3 (6)Cu1—N1—S1—C1098.8 (2)
C3—C4—C9—C8179.7 (4)C11—C10—S1—O216.9 (4)
C7—C8—C9—N2179.1 (4)C15—C10—S1—O2167.2 (4)
N1i—C8—C9—N20.9 (5)C11—C10—S1—O1144.7 (4)
C7—C8—C9—C40.1 (6)C15—C10—S1—O139.4 (4)
N1i—C8—C9—C4179.9 (4)C11—C10—S1—N1103.2 (4)
C15—C10—C11—C122.5 (7)C15—C10—S1—N172.7 (4)
S1—C10—C11—C12173.4 (4)C8i—N1—Cu1—N1i124.0 (3)
C10—C11—C12—C131.0 (8)S1—N1—Cu1—N1i29.15 (19)
C11—C12—C13—C141.3 (7)C8i—N1—Cu1—N2125.6 (3)
C11—C12—C13—N3176.7 (5)S1—N1—Cu1—N281.3 (2)
C12—C13—C14—C152.2 (7)C8i—N1—Cu1—N2i10.5 (3)
N3—C13—C14—C15175.8 (4)S1—N1—Cu1—N2i142.6 (2)
C13—C14—C15—C100.7 (7)C1—N2—Cu1—N116.0 (4)
C11—C10—C15—C141.6 (7)C9—N2—Cu1—N1173.9 (3)
S1—C10—C15—C14174.3 (4)C1—N2—Cu1—N1i179.1 (4)
C2—C1—N2—C90.7 (6)C9—N2—Cu1—N1i10.8 (3)
C2—C1—N2—Cu1168.6 (3)C1—N2—Cu1—N2i78.2 (4)
C4—C9—N2—C10.6 (6)C9—N2—Cu1—N2i91.8 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1ii0.932.503.354 (5)153
C11—H11···O3iii0.932.403.271 (6)156
C15—H15···O1i0.932.543.335 (5)144
Symmetry codes: (i) x, y, z+1/2; (ii) x1/2, y+1/2, z; (iii) x, y+1, z1/2.
 

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